Santiago has a unique take on Cuban and Caribbean cuisine, but it isn't an especially great place for dining; there are few really good restaurants, and even fewer paladares (private home restaurants). A couple of the better restaurants are outside of downtown, and it's best if you plan ahead to combine them with sightseeing. The couple of officially sanctioned paladares and the state-run restaurants (many of which are concentrated around Plaza Dolores) are nothing to look forward to. Understandably, many visitors tend to eat at their hotel restaurants -- as good an option as any. The Meliá Santiago de Cuba and Hotel Casa Granda have elegant restaurants that are worth a splurge even for nonguests (though you may want to skip the Italian restaurant La Fontana in the Meliá). Although you can only get sandwiches and simple dishes there, one of my favorite lunch spots is the open-air terrace bar at the Hotel Casa Granda. On a hot afternoon, this is the coolest place in town -- in both senses of the word -- but you should be prepared for laughably slow service. You can also get a decent pizza for CUC$4 on the 5th floor terrace of the Casa Granda. This has affordable drinks and one of the best views in Cuba: the cathedral, bay of Santiago, and the mountains beyond. Around the corner on Aguilera is the new pan.com. Its ham and cheese paninis are tastier and cheaper than those of the Casa Granda's, but there's no view.
Café Ajedrez, Calle Enramada at Felix Peña (no phone), is located in a tiered 1966 art-deco building by architect Walter A. Betancourt. The café features stylized metal tresses, art-deco lamps, and stone tables with chess boards (ajedrez). It's open Tuesday to Sunday from 10am-3pm. Another great spot, if it's not overrun with jineteros, is the atmospheric Café La Isabelica on Plaza Dolores, corner of Calle Aguilera and Calvario. The two signature coffees are rocio con gallo (coffee with rum) and the Café Isabelica (coffee, rum, and honey). The cafe is reminiscent of an old inn with darkened furniture, leather-and-hide-covered chairs, and gossiping old men. It is open 24 hours daily. Santiago's Coppelia (the national ice cream chain) is known as La Arboleda and is on the corner of Av. Garzón y Av. de los Libertadores. Get your bargain ice cream bolas here in moneda nacional. There is no entrance fee. Splurge on the seven multi-flavored scoops of the Gran Piedra dish. It is open from 10am to 10pm daily.